Cheap Flights from Charleston to Chicago
Browse current best options from Charleston. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Charleston
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Prices updated today
456 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Aug 31, 2026.)
Today’s best flight deals from Charleston to Chicago
Explore current cheapest deals departing from Charleston to Chicago
2026-09-14 – 2026-09-28
CHS - Chicago
45% AI deal score
$219
$220
Round trip
2026-11-04 – 2026-11-16
CHS - Chicago
49% AI deal score
$248
$228
Round trip
2026-10-01 – 2026-10-05
CHS - Chicago
50% AI deal score
$268
$232
Round trip
2026-11-11 – 2026-11-16
CHS - Chicago
67% AI deal score
$284
$234
Round trip
2026-09-23 – 2026-09-26
CHS - Chicago
44% AI deal score
$150
$237
Round trip
2026-09-17 – 2026-09-19
CHS - Chicago
44% AI deal score
$152
$237
Round trip
2026-09-14 – 2026-09-15
CHS - Chicago
43% AI deal score
$153
$237
Round trip
2026-09-19 – 2026-09-28
CHS - Chicago
43% AI deal score
$133
$237
Round trip
2026-09-24 – 2026-09-28
CHS - Chicago
44% AI deal score
$150
$237
Round trip
2026-10-14 – 2026-10-21
CHS - Chicago
44% AI deal score
$142
$237
Round trip
